Email Etiquette: How To Approach Someone You’ve Put “On Hold”

Dating two people simultaneously is hard (and some would say, rude!). But how do you transition from an early relationship that didn’t work out to the “second best” person? If you’re new to online dating, it can be difficult knowing how to handle these situations. Don’t worry. You’re not alone! Here’s a great question that came in this week as a comment on our post titled, “To Write Or Not To Write.”

I sent a reply saying something similar to what you suggested: “You seem nice, but I’m currently dating someone and seeing if it pans out. If it doesn’t, I’ll let you know.“ Unfortunately, it did not pan out with the first girl. How do I recover and now ask this second girl out without her feeling that she is second best? (It feels like I just closed the door on this potential date and now I am scared to open the door again).

The Situation

Our single guy wanted to see how things went with one date before going out with a second person. Now that he knows that the first person isn’t a viable candidate, he’d like to approach the second one without making her feel like she’s second best.

Opening The Door

Your goal here is to make your second choice feel like she was your first choice all along. Since you’re a caring human being, you wanted to avoid dating two women at once. You were honest to Woman #2, and while it may have stung her a bit, she should at least understand that you are trying to do right by Woman #1.

Here’s an idea for an email:

Hello again!

I hope you’re doing well and enjoying the warmer weather! A few weeks ago, you sent me an email when I was just about to go on a third date with another match. She’s a great person, but we just didn’t click. Now that I can give you my full attention, I’d love to chat. How are things going with your PhD?

Looking forward to talking with you soon.

You can do it!

Writing one of these emails is a lot like a first contact email. You’re making things personal and tied to their profile. You end the email with a question and a closing that nicely hints that you anticipate a reply. And like a first contact email, you may not get a reply. She may have moved on to someone else, be taking a break, or she may have lost interest in you.

But you never know if you don’t email, so send it!

Happy dating, geek friends.

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Since 2008, E. Foley of Geek’s Dream Girl has been helping geeks from around the world find love. She writes amazing online dating profiles for her fellow geeks and guides them through the perilous waters of the dating scene and out the other side. She's totally proud to report that she's even caused a couple geek weddings! She lives in Maryland with DaveTheGame, her adorable cats, Mr. Peanut & Don Juan, and Titania, Queen of the Cocker Spaniels. (Email e, or follow @geeksdreamgirl on Twitter.)

About The Author

e

Since 2008, E. Foley of Geek’s Dream Girl has been helping geeks from around the world find love. She writes amazing online dating profiles for her fellow geeks and guides them through the perilous waters of the dating scene and out the other side. She's totally proud to report that she's even caused a couple geek weddings! She lives in Maryland with DaveTheGame, her adorable cats, Mr. Peanut & Don Juan, and Titania, Queen of the Cocker Spaniels. (Email e, or follow @geeksdreamgirl on Twitter.)

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